title: Conversion of phenols into selenophenols: seleno Newman-Kwart rearrangement.
abstract: A 'Se'lling point: The first thermally induced OAr →SeAr migration reaction is reported, and it can be used to prepare aryl selenols in three steps from the corresponding phenols. O-aryl selenocarbamates rearrange to Se-aryl carbamates via a four-membered transition state. The aryl selenols (isolated as the diselenides) can be prepared by hydrolysis of the Se-aryl selenocarbamates.
authors.affiliation: University of Copenhagen, Department of Chemistry, Universitetsparken 5, 2100 Copenhagen Ø (Denmark) http://www.pittelkow.kiku.dk.
authors.forename: Anne
authors.initials: A
authors.lastname: Sørensen
authors.forename: Brian
authors.initials: B
authors.lastname: Rasmussen
authors.forename: Shubham
authors.initials: S
authors.lastname: Agarwal
authors.forename: Magnus
authors.initials: M
authors.lastname: Schau-Magnussen
authors.forename: Theis I
authors.initials: TI
authors.lastname: Sølling
authors.forename: Michael
authors.initials: M
authors.lastname: Pittelkow
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry; D018360:Crystallography, X-Ray; D007700:Kinetics; D008968:Molecular Conformation; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D001555:Benzene Derivatives; D002219:Carbamates; D016566:Organoselenium Compounds; D010636:Phenols; C018846:benzeneselenol
keywords: X-ray crystallography; density functional calculations; kinetics; rearrangement; selenium